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OR
1
OR
1
O
O
R
1
O
R
1
O
HO
HO
OC
14
H
29
OC
14
H
29
OR
1
OH
O
O
R
1
=
NH
3
5 or 10
NH
3
5 or 10
R =
OC
14
H
29
OH
OH
O
O
N
OC
14
H
29
HO
OH
O
S
O
OR
2
O
H
HO
O
H
N
NH
2
OH
H
O
H
NH
N
H
N
H
O
R
2
=
N
N
H
N
N
O
N
Fig. 19 Structure of cationic glycolipids described by Maslov et al.
53
Cl
Cl
R
R
R
R
N
O
N
H
OH
H
H
OH
H
HO
HO
HO
H
H
HO
H
H
R = C
14
H
29
R = C
16
H
33
R = C
18
H
37
OH
OH
OH
OH
Fig. 20 Structure of cationic glycolipids described by Mahidhar et al.
54
alkyl chain
51
or a cholesteryl chain
52
directly connected at the anomeric
position. The same research group
53
also developed a galactoside de-
rivative equipped with a polycationic chain (formally 3 charges) linked on
the nitrogen atom of an aminopropanediether (C
14
) (Fig. 19).
Cholesteryl and galactoside compounds were evaluated in transfection
assays. The cholesteryl derivatives were mixed with DOPE (1 : 1) and the
corresponding liposomes were used to prepare lipoplexes at charge ratio
up to 1. Cytosolic delivery into BHK cells
52
of FITC labelled CpG oligo-
nucleotide (FITC-ODN) led to higher transfection eciencies for piper-
idinium based lipoplexes, which reach a level of positives cells (40%)
comparable to the lipofectine reference (50%), in particular when fetal
bovine serum was used. The galactoside derivative was evaluated within a
preliminary study on BHK cells.
53
Atomic Force Microscopy (AFM) images
showed a clear DNA-compaction ability of this polycationic transfecting
agent. In terms of biological application, it was able to deliver plasmid
DNA (EGFP) with level arising lipofectamine results. As mentioned by the
authors, further work including lipoplex formulation optimisation is now
necessary to confirm the potential of this compound in gene delivery.
Mahidhar et al. described the synthesis of a series of cationic galac-
toside transfecting agents (Fig. 20).
54
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